HCID 67229347, compound → HCID 67228049, compound

HRID 1515619Notes

Reaction equation

HRID 1515619 reaction equation
[CH:1]1([CH:7]=[C:8]([C:19]2[NH:29][C:22]3=[N:23][CH:24]=[C:25]([O:27][CH3:28])[CH:26]=[C:21]3[CH:20]=2)[C:9]2[CH:14]=[CH:13][C:12]([S:15]([CH3:18])(=[O:17])=[O:16])=[CH:11][CH:10]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>[Pd].CO>[CH:1]1([CH2:7][CH:8]([C:19]2[NH:29][C:22]3=[N:23][CH:24]=[C:25]([O:27][CH3:28])[CH:26]=[C:21]3[CH:20]=2)[C:9]2[CH:14]=[CH:13][C:12]([S:15]([CH3:18])(=[O:17])=[O:16])=[CH:11][CH:10]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 67229347HCID 67229347, compound

Product 1

HCID 67228049HCID 67228049, compoundYield 76.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 2-[2-cyclohexyl-1-(4-methanesulfonyl-phenyl)-vinyl]-5-methoxy-1H-pyrrolo[2,3-b]pyridine (80 mg, 0.19 mmol) and 10% palladium on activated carbon (50 mg) in methanol (200 mL) was heated at 50° C. under hydrogen (50 psi) for 6 h. The mixture was cooled to room temperature, the catalyst was removed by filtration and washed with ethyl acetate. The filtrate was concentrated in vacuo and purified using a Waters automated flash system (column: Xterra 30 mm×100 mm, sample manager 2767, pump 2525, detector: ZQ mass and UV 2487, solvent system: acetonitrile and 0.1% ammonium hydroxide in water) to afford 2-[2-cyclohexyl-1-(4-methanesulfonyl-phenyl)-ethyl]-5-methoxy-1H-pyrrolo[2,3-b]pyridine (60 mg, 75%) as a light yellow solid: LC/MS m/e calcd for C23H28N2O3S [M+H]+ 413.56, observed 413.3.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customthe catalyst was removed by filtration
  3. washwashed with ethyl acetate
  4. concentrationThe filtrate was concentrated in vacuo
  5. custompurified

Sources & evidence

ORD record
ord-ab594f8c884b472db395c6115922a486
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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